[Seanlet]

I've been studying the history of the various routes to making sertraline. I was amazed the route that won the 2002 Green Chemistry award. No dehydrating agent because the ketimine isn't soluble in ethanol. I wondered if sodium borohydride could simply effect reduction to the final compound. I also looked at newer routes and many form the hydrochloride salt of the ketimine.

Can anyone tell me how stable these ketimine salts are? Are they still moisture-sensitive.

You see, I'm trying to work out if it's possible to design a route that needs no heating or cooling & no pressure-vessels. I KNOW NaBH4 isn't the cheapest way to reduce, but with energy costs rising so fast, maybe soon it will be the cheapest... Most use a nitrogen blanket but in award-winning route, is it O2 or CO2 they need to keep out?

I figured if they used isopropanol as the solvent, transfer hydrogenation might work?

The way I thought that heating to form the ketimine could be avoided is by the use of MCM-41-SO3H as described in 'Efficient synthesis of imines by MCM-41-SO3H nanocatalyst'. Expensive, so I would need to find a way to recover as much as I possibly could to keep down the theoretical cost.